Home Cover Story Bewitching Brews & More: Let the Ghoul Times Roll in Winchester

Bewitching Brews & More: Let the Ghoul Times Roll in Winchester

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By Chad T Walker

Downtown Winchester is alive and well, just in time for Halloween season.  A substantial number of new businesses have sprouted post-pandemic, with a vibrant landscape populated by restaurants, bars, the Historic Leeds Theatre, and even a retail spot dedicated solely to the art of making cheesecake. Known as the birthplace of both beer cheese and Ale8, seasonal festivities and decorations surrounding downtown may add a third specialty to Winchester’s already purely Kentucky lineage:  Halloween.

Longtime downtown staple Mason’s on Main (70 South Main Street), co-owned by Mason Rhodus and Jeffrey Hale, is getting set for the Halloween season. A large black cat atop their awning and redecorated storefront balances out the already finely curated collection of antiques and custom bow ties, each one made by Mason himself.  When asked about Halloween-time hauntings, Mason responded in the affirmative.  

“Yes, my building is haunted by two spirits,” said Mason. But he’s confident that the things that go “bump in the night” won’t deter would-be visitors to one of Kentucky’s most picturesque downtowns.

“Our draw is all the historic buildings on our Main Street.  It’s like something from a Hallmark movie set.”  

One of downtown’s newest additions is Cheesecake and Company (39 South Main Street), owned by Mikaela Bush, who began her life as a baker when she opened an “honor system” venture in rural Ohio, affectionately called the “Cheesecake Cabin.”  She decided to relocate to Winchester’s booming downtown to open a more permanent brick-and-mortar spot. Although just a year into owning her slice of Main Street, she earned the “Business of the Year” award from the Winchester Chamber of Commerce.  Not one to shy away from a challenge, Mikaela plans on offering cheesecakes to match the spooky season.

Just around the corner is The Engine House Pub and Pizza Parlour (9 West Lexington Avenue), owned by Jill and Chad Walker.  Featuring pizza, calzones, local beers and craft cocktails, Engine House has been a downtown staple for decades, predating Jill’s ownership of the business to when she worked there in high school under original owner and beer cheese royalty, Bob Tabor.

Jill decorates the restaurant seasonally, with her Halloween display already in full swing. Featuring a giant spider and web, creepy photos and two continually smoking cauldrons on the bar, Jill transforms Winchester’s original firehouse into a Halloween work-of-art.

“Halloween is the holiday that best suits the one hundred thirty-nine year old building.  Wooden walls, warm interior, dim light and history provide a spooky but friendly ambiance,” said Jill.

When asked if she could share an experience from the haunting season, Jill said, “It’s Halloween every day.  Staff have reported hair-pulling, being called by name, disembodied voices coming from electronics and captured on cameras, as well as mysterious crashing sounds and objects falling without explanation.  Although we feel our spirits are friendly and playful, it’s enough to keep you hair on end.” 

Wildcat Willy’s has rebranded under its new name, Regeneration Distilling Company (31 East Broadway).  Focusing their direction as a farm-to-bottle distillery, Regeneration utilizes locally grown products to produce Kentucky’s finest artisanal spirits.  As one of many participants in the Annual Zombie Pub Crawl, Regeneration’s unique products are a staple for any Halloween party, with Sweet Potato Moonshine, Apple Pie Moonshine and Boone’s Settlement rye whiskey rounding out some of the favorites.  

The folks at Regeneration plan on hosting a party in an old log cabin where, “all the whiskey is aging in a tobacco barn right behind it, by the goats,” said owner Laura Freeman.  

As far as the creepy crawly parts of Winchester, Laura says they have ghosts aplenty.  “I do have a (personal) ghost story, but it is out here in the country, in one of our cemeteries.”  She went on to say that downtown during Halloween is especially creepy.  “You can feel the ghosts,” she said.

Whether you are a ghost or goblin, an undead or pirate, or just someone who enjoys the fall festivities, head over to Winchester, the small town King of Halloween, where you can enjoy live music, candy, good food and drink, and a bustling downtown.  Who knows, maybe we will “scare” you there.



Halloween Main-ia, a downtown Winchester staple since 1996, will be returning October 28, from 6-8 pm. Spooky treats, free inflatables and balloon twisting, and food trucks will fill the streets. Dress up in your favorite costume and check out all that downtown Winchester has to offer.

Fanny Fest: A Cider Festival Honoring Fanny Cole, October 14, 12-5pm. This festival will be honoring Fanny Cole, Winchester’s first legal cider maker. “Fanny flights” will be offered benefitting local scholarships in partnership with the Winchester Black History and Heritage Committee.

Pride and Inclusion Festival hosted by ProudTown Inc., October 21, from 1-6pm. Winchester’s first Pride and Inclusion Fest with vendors, inflatables, food, and fun for all people.

And finally, the Zombie Pub Crawl returns for its third year.  Hosted by the Engine House, this year the theme will alter slightly to allow even more entrants than just the “undead.”  Set for October 20, the weekend before Halloween.  Check Engine House’s facebook page for tickets and details.

This article appears on pages 8-9 of the October 2023 issue of Ace. To have the digital edition delivered to your inbox each month, click here.